SEMESTER 20224 ASSIGNMENT 1 CHM557

ORGANIC CHEMISTRY

ASSIGNMENT 1

SPECTROSCOPY
SEMESTER OCTOBER 2022 –
FEBRUARY 2023

Name : AHMAD ZAKWAN BIN KASSIM

Student ID : 2021886994

Group : AS2533A2
 ASSIGNMENT CHM557
OCT2022 – FEB2023

1. The following is the IR spectrum of alcohol, which has the molecular formula C2H6O.
Select three (3) significant peaks associate with the alcohol from the given spectrum.
State the wavenumber and the bond associated with each peak you selected.

(6 mark)

2. The IR, 1H NMR and 13C NMR spectra of carbonyl compound R which do not react with
Tollens’ Reagent are shown below. The molecular formula for compound R is C13H10O.
i) Identify three (3) important absorption peaks on the IR spectrum and indicate
the bond and wavenumber associated with each peak.
ii) Elucidate the structure of compound R and assign each peak in the 1H and 13C
NMR spectra.

(14 mark)
3. Isopropyl alcohol can be oxidized to acetone via hot oxidation of sodium dichromate
i) Sketch a predicted 1H NMR spectrum for isopropyl alcohol with signals in
estimated chemical shift ranges and with expected splitting. (4 mark)
ii) Give the integral values as a whole number ratio for the signals in the 1H NMR
spectrum of isopropyl alcohol (2 mark)
13
iii) How many C NMR signals would you predict for isopropyl alcohol? (1 mark)
iv) State the oxidizing agent for the above reaction other than sodium dichromate
(2 mark)

4. Two aromatic compounds (A and B) have the same molecular formula of C9H10O.
They both show infrared spectra with a strong absorption at 1710 nm-1. Determine
the structure of the compounds if the show the following 1H NMR data.

Compound A Compound B
4.0 ppm, singlet, 3H 0.98 ppm, triplet, 3H
3.7 ppm, singlet, 2H 2.3 ppm, quartet, 2H
7.4 – 7.6 ppm, multiplet, 5H 7.4 – 7.6 ppm, multiplet, 5H

(6 mark)
5. Compound E with a molecular formula of C4H8O, gives a positive iodoform test and
has the following 1H NMR

Compound E
Triplet, 1.3 ppm
Singlet 2.1 ppm
Quartet, 2.7 ppm

i) Suggest the structure of E (2 mark)

ii) Outline an equation for the reaction between compound E and the Iodoform
Test (3 mark)